A Brief Lesson on Managing Designers

It’s Raining in Los Angeles

“I don’t want to be a manager anymore,” I say to my boss. A law in business is to never break bad news on a Friday unless something needs to be dealt with in the dark, and I feel like I’m declaring my guilt with this slip through the back door. I’m asking to quit the management role that I petitioned for almost a year ago.

“I’m disappointed because I think you’re giving up on this too soon… You’re actually great at this, Freddie,” she says. I think my boss is modest but by stepping away from management I’m letting the full weight of the design team fall upon her.

“At least tell me why,” she says. I pause, and don’t know what to say next. There are too many reasons to list, but none of them clearly describe why I’ve started to loathe this job. I reach for the only words that make sense.

“Managing is a craft to be mastered,” I say.

What I’m trying to explain to her is that I didn’t know what I was getting myself into when I asked for this job. All I knew was that I wanted to share everything I had experienced in the past 10 years as a designer with my new intern. After single-mindedly clawing my way into a well-compensated creative position, I figured that I knew the roadmap, and could pass on my knowledge so that someone else could do the same. Once I achieved that, I figured that I knew the roadmap to instill my knowledge so that someone else could do the same. But after a year of effort, I am ready to accept I have not yet mastered this particular craft. Another year after this meeting, the lessons I learned during my time as a manager have finally sunk in enough for me to write them down.

What follows is a distillation of the lessons I learned in my time managing designers. If you’re just starting to manage, I don’t envy you—you just signed up for the hardest job I’ve ever experienced. It was deeply lonely for me, even as I was surrounded by caring mentors, so I can’t even imagine what you’re feeling right now. If you stop reading right now, at least take this with you: Experience, keen observation, and enough fucks given will eventually teach you how to do this job well, just as they taught you design.

My goal is to speed up that process exponentially.

“Managing is a craft to be mastered.”

Being skilled in a craft is not art, but it can look that way to the uninitiated. Famous leaders and managers in tech, present and past, seem almost divine to us, but their craft is within reach. I found that there are three major skills that make up the craft of being great manager.

First, they have grasped that people are not to be designed but to be pruned through the environment they create. Second, they can seamlessly switch between a Top Down and Bottom Up approach to management. And third, they’ve mastered the timing of their advice.

Being adept in each of these skills will allow you to grow into your own management style, and one day the ones that you take care of might even see you as divine. Good work will happen all around you, and only the best designers will want to be on your team. Tell them that it’s not magic. This is a craft just like their job, and nothing more.

No, You’re Not a Designer Anymore

As a freshly promoted manager with one direct report, I didn’t know what I was getting myself into. My first stumble came in the first few weeks. My new designer had just moved into the product design department from another part of the organization. She definitely had taste and thankfully, enough passion to finish projects. I had lucked out, because I couldn’t teach those.

While she was working on her first product design assignment, I would occasionally look over her shoulder and try to contribute new and wild ideas that she was clearly missing. She was like a blank artboard and I was determined to design her, but immediately I noticed that something was way off. A clear cycle emergered: she would listen intently to my advice, but her work would get worse as she attempted to incorporate my feedback.

On and on we went. I would point out what was wrong in her designs and she would go fix them, and the product would lose more focus. I wanted to scream. It felt like I was trying to design in Sketch with a potato moving my cursor. Making rectangles hurt. Putting type on the screen was excruciating. Moving elements around pixel by pixel made me want to pull my hair out. A year later, I realized that I had failed at all three areas of being a great manager all at once. At the time though, it felt like I had tripped in the dark and fell into a rose bush—this was clearly hurting but I couldn’t see why. Here are all three of my mistakes:

I was trying to design a person like how I would design apps on my computer. She was not a boring static rectangle. She had her voice that I needed to bring out.

I tried to manage her in the way I liked to be managed. I would point out what was wrong and let her find her own unique solutions. She was still too green.

I constantly gave her tightly packed advice that only made sense with a deep understanding of the craft of design.

An understanding of these three issues and how you can avoid them will make you great at this job.

Till the Soil

It’s tempting to rely on your design training when you become a manager for designers. I know because that’s what felt natural to me, but you don’t design people—this is the wrong way to look at the job. People are not functions and they are not artboards. You can’t give the same advice to 10 different people and expect the same outcome for each person. Rather, your job is to design the environment. It’s the main area that you have control over and I never saw this.

I’m not talking about an abstract concept, the environment is tangible. It’s where everyone is sitting, how and when your team meets, the music that you play, the jokes or seriousness that you cultivate, the types of computers and monitors they have, the books around your team, the posters, your voice, laughter, how and when you critique, and anything else that is not part of your standard design software.

You are also their shield from the rest of the organization. Inbound requests come to you and no one ever notices the environment that you’ve designed for them. They love to come into work and they feel the most creative around you and the rest of your team. Good work is being done even if you’re not there, simply because the environment works. You are constantly pruning the environment to facilitate better work. New people are added to the team and you continue tilling the soil by tweaking those environmental variables.

I focused on my direct report, but I never noticed the environment as something I could control.

Founders at startups do this naturally because there’s no other choice. You’re in close proximity with everyone and you want work to be enjoyable for everyone (as long as you’re not a complete sociopath). Eventually, the environment you’ve created turns into culture, and then myth.

Top Down and Bottom Up Methods

There are two major theories about managing that I discovered. The first holds that you can design through someone else’s hands, and the second that you can create the conditions where others flourish. If you’re thinking to yourself that the latter is the best way because it sounds the nicest, you’re dead wrong. From personal experience I know that sticking to only one of these methods will produce the same outcome–people struggling to do great work with a one size fits all method.

Top Down: Designing Through Someone Else’s Hands

Designing from the top down feels brutal and egotistical, right? Why would you force someone to design exactly like you? If you use this method, it will feel as if you grew two new arms and your output doubled. It’s wildly addicting to see your vision come to fruition so quickly. I suspect that this is the major reason why people feel like they need to start managing.

A pro to this approach is that it’s the most direct way to teach something new to a person. All the nitty gritty details of what you’ve learned as a designer are embedded in your brain as second nature and it’s difficult to effectively teach that without a clear understanding of how you work. Imposing your methods directly will instill this knowledge into your designers, as well.

A con to this approach is that skilled people with at least 3-4 years of experience may feel like resources to be used, and if you insist on forcing your vision through their hands then experienced designers will eventually resent you and leave. One other major downside of always being in this mode is that the output and vision of your team will stagnate over time. Under your watchful eye, the same things will be created everyday. When the world changes, and it will, you’ll be left far behind. Trying to switch to another management style late in the game will reveal the weaknesses in your own design and force you to find innovators to replace yourself.

Bottom Up: Design the Conditions Where Others Flourish

Letting your designers take the reins feels nicer, even altrusitic. I would recommend this approach when managing people that have already come into their own. They have found their voice in their work and now your job is to make sure that it continues to grow. Your advice and mentorship at this level means pointing out things that they have clearly missed and letting go of control at most points.

If done right, the creativity and divergent thinking that emerges from this can create a quality work that would make Pixar jealous. With more autonomy, your team works together to bring out each others voices and you are there to mostly observe with occasional quick feedback.

But this approach can be a lazy way to get results, and paradoxically can be a more egotistical way to manage than the first one. You’re trusting your designer to deliver discoveries, and offloading the growth of the product that you are ultimately responsible for. I’ve noticed that many managers opt for this approach when they want everyone to like them. They want to be the cool teacher, in charge and looked up to.

Which to Use?

So can you use both approaches for junior level and senior level people? Hell yes, but figuring out the perfect moment for each will take you time. My rule of thumb is that younger designers don’t know much about the day-to-day cadence of working through tough ideas, so you should give them more guidance with a Top Down approach. More senior designers already know how to do their job, so it’s better for you to leave them to it and point out small details that will push them towards their goals. But even senior designers can sometimes benefit from watching you work on their file directly. And sometimes, you must see your juniors struggle for a few days so they can develop their own strategies for problem solving.

To get the most out of your people, try to balance these two. My own designer was too green for a Bottom Up approach and my open-ended feedback confused her. I was thinking of myself too much when I only used this approach—I wanted everyone to like me.

After days of our frustrating work cycle, I finally just copied her file and went to work on it as if I was the designer again. I told her to watch everything I did. I rarely opened by mouth once I was back in the zone and it felt great to return to designing, like coming back to a long lost friend. I copied artboards. Created crazy elements. Pushed the visual language beyond what we could ship, and I kept iterating. With every move, I tried to push myself through this insane product maze that she had built for herself. Finally, we both understood the key to this early stage of her learning process:

Work like me for now but we’ll eventually find your voice together.

Though I couldn’t put this lesson into words at the time, my Hail Mary saved the project, our jobs, and our sanity. I used both approaches with her from that point forward and I saw a jump in confidence and skill level that I have never come close to in my own career.

I’m still proud of her for that project.

Chunking Knowledge

As a new manager, it is tempting to give advice first, every single day, and every opportunity you get. Avoid this trap, because there is no context for your directions. Focus on the environment and practice both management styles first—focus on what you can control directly before you dive into imparting your knowledge. While the best advice comes with depth learned through personal experiences, this makes it incredibly difficult to put into words. It has taken me years to figure out how to share the bits of wisdom I’ve collected. It’s not impossible, but it is fucking hard.

When you begin to master a craft, you naturally start to condense data into smaller chunks that you can more easily communicate with others at your level. One word can describe an entire array of concepts. Here’s an example:

“Your colors are loud and that icon has too much weight.”

If we have the same understanding of design fundamentals, you understand me perfectly, but I’ve just lost the layperson reading this. They’re not even seeing the same sentence we’re seeing! There are whole paragraphs conveniently tucked away into that sentence that we both understand because we can pull from our shared knowledge.“Loud” and“weight” are loaded concepts.

These two concepts are central to the visual language that we’ve learned through decades of graphic design and based on principles that can be traced back all the way to cave paintings. These concepts have been passed from Ancient Greek artists, to Renaissance painters, to the French Impressionists, to cool Andy Warhol, and finally to you and me. There is a deep amount of knowledge that we’ve accumulated through the generations and somehow, we’ve internalized most of it. Understanding how colors sound or taste, or how visuals can have gravity, weight, and velocity; all of this took me years to figure out. This is a clear translation of that sentence:

“The colors in that icon have risen to a saturation range where it’s competing with the rest of the composition. It would be better to mute that color down in saturation to avoid the perceived garishness that users will find in it. It’s going to take too much attention. Also, that icon’s shape is much too solid compared to the rest of the composition and you should think about the weight of it’s lines just like you do with type. Make the lines thinner to create a better appearance of lightness.”

I know you understood that.

Now that we’ve laid it out in plain english, why should we even bother to use the short example? Why not just clearly spell it out every single time to everyone? Why not just give verbose advice to everyone we see? Go back to the Top Down vs Bottom Up methods. I’ve done something with both of these pieces of advice that you probably haven’t noticed yet.

“Your colors are loud and that icon has too much weight.”

This tells the person exactly what’s wrong without going into too much detail about what they should fix. I can concisely convey information and the benefit is that a designer will use their experiences to uniquely solve this problem. This is an excellent example of Bottom Up advice. How about the verbose one?

“The colors in that icon have risen to a saturation range where it’s competing with the rest of the composition. It would be better to mute that color down in saturation to avoid the perceived garishness that users will find in it. It’s going to take too much attention. Also, that icon’s shape is much too solid compared to the rest of the composition and you should think about the weight of it’s lines just like you do with type. Make the lines thinner to create better appearance of lightness.”

This detailed piece of advice now serves someone who hasn’t learned our advanced chunking methods yet. They can’t hear loudness in their inner ear when they look at work. They still can’t feel the weight of objects and they damn sure can’t manipulate it yet without clear instructions. Both look like the same piece of advice but they serve very different functions.

I hope I blew your mind right now. Now that you know how to articulate your advice, how can you learn to give it at just the right time?

Timed Advice

Timing your advice perfectly comes with experience as well but I’ve found that advice works best in two moments: in the middle of a project and after it ends.

It’s tempting in the beginning, but you’re doing a disservice to your people. I’m not talking about reframing the problem to come up with new approaches, I’m talking stroking your ego with stories of similar projects that you’ve conquered. Advice can be masturbatory without a real problem that it’s focused on.

The prime time for advice is when designers are in the middle of a project. Everyone will eventually be stuck and since you’re not deep in the weeds like they are, your advice can cut through and illuminate areas that they’ve missed. When you’re in the middle of the project, there’s nothing to talk about except the problem. Suddenly, advice is easily framed around real problems, not the conceptual onces that you think will pop up in the beginning.

The worst time for advice is near the end of a project. God help you if you do this often because all you’re doing is throwing chum in a pool full of agitated sharks. You can stop a project in its tracks with bad advice by making designers second guess themselves and ultimately do a bad job. Again, nothing is black and white so if you truly see something wrong that everyone has missed, for the love of God, just say it. Advise on what is missing and let them scramble to fix it. Take note that it might serve you better to give more prescriptive advice next time, and try to do it in the middle of projects to catch those mistakes earlier.

A great time for advice is after a project is finished. There are no deadlines at this point and everything has shipped. You can point out mistakes, but the great thing is that no one can do anything about it. All they can do is lick their wounds and move on to the next project. This is exactly how you became who you are, by learning from your own mistakes. Having gone through the process, they can understand your advice in the context of their own struggles. Your words can finally sink in after they’ve gone through the valley of shadow and death.

With me and my first direct report. I made every single mistake in giving her advice. I offered way too much of it too quickly. I was eager to impart my knowledge to her but the timing wasn’t right. It was like she was hearing a podcast of world history as she was trying to cook a 5 star meal—there was too much information and none of it was helping her to make that perfect dish so she was forced to ignore most of it. When I pulled back my advice and focused it on the problems and the post-mortem, I saw a world of difference.

It Stopped Raining

After I resigned my role as Product Design Manager, I went home and had a drink. I was embarrassed, happy, and incredibly excited. Yet again, I had pushed myself past what I thought I could accomplish, and even though I had failed this time, I felt I had learned some valuable lessons. That afternoon, I wrote a new manifesto as I drank my I’m-done-being-a-manager beer:

I will never design people—I will design the environment.

I will never use a one size fits all method to management—I will do both Top Down and Bottom Up.

I will only give advice in the middle and end of projects.

I’m not managing anymore but I’m confident that I’ll get back into again someday with the right motivations. For now, I wanted to get back to creating. On the Monday after I quit my role and I became an individual contributor again, I opened Framer X. I started to devour every single piece of information on it. I spent days working, and didn’t talk to anyone for a while. In part my solitude was out of embarrassment, but I was also in awe of learning Framer X. It felt right to be back in the weeds.

It wasn’t raining in LA anymore, and when the sun came back up, I noticed I had changed. I was scarred, but a tiny bit wiser. I hope to help you find the wisdom without the scars, dear reader.

– Freddie Iboy

Writer’s Note

For my first blog post, I figured that I would start with a big failure of mine that I’ve never talked about until now. I’d like you to get to know me as a working designer—I’m failing all the time but I’m pushing forward. The combination of obsession and finding luck has somehow (against all odds) brought me on an incredible journey to help build some of the best experiences in the world. I honestly wish this writing can bring the same for you.